Sell financed investment in Red Lodge Mt and buy cash in Galena Ill or Door County?

[Jane Shehan]

We currently own an STR in Red Lodge Mt. We have a $180K loan on it. The rentals are paying the holding costs on it so far (taxes and insurance are high in this market). We are self managing it as we live fairly close. We are retiring in a couple of years to the Midwest to be closer to family. Should we sell the Red Lodge house and pay cash for another rental, albeit in a lesser market? Galena and Door County are possibilities, as is Rochester Mn which is fairly close to our farm in Iowa. We would have around $300K cash. I love the idea of being out of debt but am a bit hesitant about getting out of the Rocky Mountain national park market, as we would never be able to get back in. Passive income is important but future value is as well and it seems to me that Red Lodge Mt is the winner that regard. Thoughts?